IE790154L - Process for preparing a high ratio of cis 3-(2, 2,¹2-trichloroethyl) -2, 2-dimethylcyclopropane-1- carboxylates - Google Patents
Process for preparing a high ratio of cis 3-(2, 2,¹2-trichloroethyl) -2, 2-dimethylcyclopropane-1- carboxylatesInfo
- Publication number
- IE790154L IE790154L IE790154A IE15479A IE790154L IE 790154 L IE790154 L IE 790154L IE 790154 A IE790154 A IE 790154A IE 15479 A IE15479 A IE 15479A IE 790154 L IE790154 L IE 790154L
- Authority
- IE
- Ireland
- Prior art keywords
- dimethylcyclopropane
- trichloroethyl
- cis
- carboxylates
- preparing
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- NZWWZHKTQANWRM-UHFFFAOYSA-N 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(CC(Cl)(Cl)Cl)C1C(O)=O NZWWZHKTQANWRM-UHFFFAOYSA-N 0.000 abstract 1
- DKFGXLPITKDNNE-UHFFFAOYSA-N 4,6,6,6-tetrachloro-3,3-dimethylhexanoic acid Chemical compound OC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)Cl DKFGXLPITKDNNE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000006184 cosolvent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002728 pyrethroid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A process is described whereby esters of 3-(2,2,2-trichloroethyl) -2,2 - dimethylcyclopropane - 1 - carboxylic acid are prepared predominantly in their cis isomer form. The process comprises treating a 4,6,6,6-tetrachloro-3,3-dimethylhexanoate with an alkali metal tert-alkoxide under controlled conditions of temperature in the presence of a defined solvent-cosolvent mixture. The products of the process are intermediates in the production of pyrethroid insecticides.[EP0003683A2]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/877,151 US4166064A (en) | 1978-02-13 | 1978-02-13 | Process for preparing high cis 3-(2,2,2-trichloroethyl)-2,2-dimethylcyclopropane-1-carboxylates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE790154L true IE790154L (en) | 1979-08-13 |
| IE48059B1 IE48059B1 (en) | 1984-09-19 |
Family
ID=25369369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE154/79A IE48059B1 (en) | 1978-02-13 | 1979-01-30 | Process for preparing high cis 3-(2,2,2-trichloroethyl)-2,2-dimethylcyclopropane-1-carboxylates |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4166064A (en) |
| EP (1) | EP0003683B1 (en) |
| JP (1) | JPS6030300B2 (en) |
| CA (1) | CA1125772A (en) |
| DE (1) | DE2963657D1 (en) |
| DK (1) | DK57879A (en) |
| HU (1) | HU182649B (en) |
| IE (1) | IE48059B1 (en) |
| IL (1) | IL56508A (en) |
| IT (1) | IT1113023B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1561502A (en) * | 1975-07-22 | 1980-02-20 | Kuraray Co | Y-lactone derivatives |
| IL56400A (en) * | 1976-09-21 | 1984-07-31 | Roussel Uclaf | Alpha-cyano-3-phenoxybenzyl and 3,4,5,6-tetrahydrophthalimidomethyl esters of 2,2-dimethyl-3-(1,2,2,2-tetrahaloethyl)cyclopropane-carboxylic acids,process for preparing them and insecticidal,acaricidal and nematocidal compositions containing them |
| DE2819788A1 (en) * | 1978-05-05 | 1979-11-08 | Bayer Ag | Benzyl esters with fluorine-substituted ether and / or thioether groups and their use as insecticides |
| US4532258A (en) * | 1978-07-11 | 1985-07-30 | Kuraray Co., Ltd. | Certain cyclopropane carboxylic acid esters and their pesticidal use |
| EP0010859B1 (en) * | 1978-10-31 | 1982-12-01 | Imperial Chemical Industries Plc | Process for the preparation of cyclopropane carboxylic acid esters |
| DE2852275A1 (en) * | 1978-12-02 | 1980-06-19 | Basf Ag | NEW ESTER FOR PEST CONTROL |
| EP0022608B1 (en) * | 1979-07-13 | 1983-07-06 | Imperial Chemical Industries Plc | Process for the preparation of cyclopropane carboxylic acid esters |
| EP0051355A1 (en) * | 1980-10-08 | 1982-05-12 | Imperial Chemical Industries Plc | An improved process for the preparation of certain cyclopropane pyrethroid intermediates having a high cis-content |
| FR2499979A1 (en) * | 1981-02-13 | 1982-08-20 | Roussel Uclaf | PROCESS FOR EPIMERIZING TRANS CHRYSANTHEMIC ACIDS |
| EP0064781B1 (en) * | 1981-04-30 | 1984-05-23 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of cyclopropane compounds |
| GB2127012A (en) * | 1982-09-22 | 1984-04-04 | Shell Int Research | Process for the preparation of cyclopropane compounds |
| GB0017617D0 (en) * | 2000-07-18 | 2000-09-06 | Zeneca Ltd | Chemical process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1269127A (en) * | 1960-06-20 | 1961-08-11 | Rhone Poulenc Sa | Process for preparing chrysanthemum acid |
| IN142702B (en) | 1974-09-10 | 1977-08-20 | Sagami Chem Res | |
| GB1498931A (en) | 1975-02-12 | 1978-01-25 | Sumitomo Chemical Co | Tetrahalopentyl ketone derivatives processes for producing them and their conversion to beta-dihaloethenylcyclopropane derivatives |
-
1978
- 1978-02-13 US US05/877,151 patent/US4166064A/en not_active Expired - Lifetime
-
1979
- 1979-01-26 IL IL56508A patent/IL56508A/en unknown
- 1979-01-26 CA CA320,323A patent/CA1125772A/en not_active Expired
- 1979-01-30 IE IE154/79A patent/IE48059B1/en unknown
- 1979-02-09 EP EP79300203A patent/EP0003683B1/en not_active Expired
- 1979-02-09 DE DE7979300203T patent/DE2963657D1/en not_active Expired
- 1979-02-12 DK DK57879A patent/DK57879A/en not_active Application Discontinuation
- 1979-02-12 HU HU79FE1038A patent/HU182649B/en unknown
- 1979-02-12 IT IT20137/79A patent/IT1113023B/en active
- 1979-02-13 JP JP54014392A patent/JPS6030300B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT7920137A0 (en) | 1979-02-12 |
| HU182649B (en) | 1984-02-28 |
| IT1113023B (en) | 1986-01-20 |
| IL56508A0 (en) | 1979-03-12 |
| IE48059B1 (en) | 1984-09-19 |
| EP0003683A2 (en) | 1979-08-22 |
| EP0003683B1 (en) | 1982-09-15 |
| DK57879A (en) | 1979-08-14 |
| DE2963657D1 (en) | 1982-11-04 |
| EP0003683A3 (en) | 1979-09-05 |
| US4166064A (en) | 1979-08-28 |
| IL56508A (en) | 1982-08-31 |
| CA1125772A (en) | 1982-06-15 |
| JPS54115352A (en) | 1979-09-07 |
| JPS6030300B2 (en) | 1985-07-16 |
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